Synthesis and absolute configuration of hormone α1

Yajima, Arata; Qin, Yong; Zhou, Xuan; Kawanishi, Naoki; Xiao, Xue; Wang, Jue; Zhang, Dan; Wu, Yi; Nukada, Tomoo; Yabuta, Goro; Qi, Jianhua; Asano, Toshiki; Sakagami, Youji

doi:10.1038/nchembio.74

Cited by 35 publications

(23 citation statements)

References 10 publications

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“…92) Qin's group developed a chiral synthon approach to the asymmetric synthesis of 1 (Scheme 6 [3]). 93) The addition of 65 to lithium salts of 66 generated by tin/ lithium exchange yielded 67. After removing the silyl protecting group, saturation of the double bond and subsequent Swern oxidation of the two hydroxyl groups afforded C1-C8 fragment 68.…”

Section: Synthesis Of Phytophthora Mating Hormonementioning

confidence: 99%

“…94) Our group succeeded in stereoselective synthesis of 1 using Sharpless asymmetric dihydroxylation as a key reaction (Scheme 6 [4]). 93) Halogen-metal exchange of (R)-citronellyl iodide (73) with t-BuLi, followed by coupling with aldehyde 74, afforded 75. After conversion of 75 to allylic bromide 76 in several steps, sulfone coupling of the bromide with sulfone 77, followed by desulfonation, afforded 78 with the full carbon skeleton of 1.…”

Section: Synthesis Of Phytophthora Mating Hormonementioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Microbial Signaling Molecules and Their Stereochemistry-Activity Relationships

Yajima

2011

Bioscience, Biotechnology, and Biochemistry

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Microbial signaling molecules such as autoinducers and microbial hormones play important roles in intercellular communication in microorganisms. Information transfer between the individual cells of a microorganism is one of the most important biological events among them. Researchers often suffer from extremely low levels of microbial signaling molecule contents, which prevent them from understanding chemistry and biology of intercellular communication in microorganisms. Chemical synthesis is a powerful tool to obtain sufficient amounts of sample and to clarify the structure of a molecule. This review focuses on the synthesis and stereochemistry-bioactivity relationships of five microbial signaling molecules, Vibrio cholerae autoinducer-1 (CAI-1), AI-2 precursor (DPD), an acylhomoserine lactone from Rhizobium leguminosarum (small bacteriocin), a diffusible extracellular factor of Xanthomondas campestris pv. campestris, and Phytophthora mating hormone α1.

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Section: Synthesis Of Phytophthora Mating Hormonementioning

confidence: 99%

Section: Synthesis Of Phytophthora Mating Hormonementioning

confidence: 99%

Synthesis of Microbial Signaling Molecules and Their Stereochemistry-Activity Relationships

Yajima

2011

Bioscience, Biotechnology, and Biochemistry

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“…Although the chemical yield was very low, 1 H NMR analysis suggested that 7 was stereochemically pure. The t-butyldimethylsilyl (TBS) group of 7 was removed under mild conditions to prevent the epimerization of the chiral center (Yajima et al, 2008) to give 8. Finally, the hydroxyl group of 8 was oxidized under mild conditions (Yajima et al, 2007b), and the chiral auxiliary group was carefully removed by LiOH to give the desired (S)-2.…”

Section: Synthesis Of Callosobruchusic Acidmentioning

confidence: 99%

Contact Sex Pheromone Components of the Seed Beetle, Callosobruchus analis (F.)

et al. 2010

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Callosobruchus analis (Coleoptera: Chrysomelidae: Bruchinae), found throughout tropical Asia and Africa, is a pest of stored legumes. Previous work has shown that females of this species produce a contact sex pheromone that elicits copulatory behavior in males. Comparisons of copulatory activity between any two of four congeneric species suggest that the contact sex pheromones are species specific. In laboratory bioassays, male C. analis exhibited copulatory behavior to a female dummy to which a crude extract of virgin females was applied. The extract had been collected by a filter paper method and was purified by acid-base partition and chromatographic techniques. Gas chromatography-mass spectrometry (GC-MS) analyses of active fractions revealed that the active compounds were 2,6-dimethyloctane-1,8-dioic acid (1) and callosobruchusic acid, (E)-3,7-dimethyl-2-octene-1,8-dioic acid (2), previously identified as contact sex pheromones of Callosobruchus maculatus (F.) and C. chinensis (L.), respectively. The stereoisomeric and chemical compositions were determined by the 2D-HPLC-Ohrui-Akasaka method as (2S,6R)-1:(S)-2=1.8:1, which meant that both compounds in C. analis were stereochemically pure, unlike the case of C. maculatus and C. chinensis. An examination of the influence of synthetic pheromone compounds on male copulatory activity revealed that (2S,6R)-1 is the main component, and that (S)-2 has an additive effect. In the examination of the stereochemistry-activity relationship, no copulatory behavior was elicited by (2R,6S)-1, and, furthermore, the enantiomer significantly masked the pheromonal activity of (2S,6R)-1. Glass rod dummy assays also suggested the presence of synergists. These results could elucidate the specificity of mate recognition in C. analis.

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“…To control the sexual reproduction of Phytophthora, we previously determined the chemical structures of two signaling molecules, namely, hormones α1 and α2, which stimulate sexual reproduction in heterothallic species. [6][7][8] The asexual cycle is the driving force of rapid polycyclic epidemics in crops and forest trees during the *Corresponding author. E mail: qijianhua@zju.edu.…”

Section: Introductionmentioning

confidence: 99%